可见光诱导的共轭磺酰胺串联脱砜/环化反应

doi:10.11944/j.issn.1000-0518.2017.11.170054

摘要/Abstract

摘要：

发展了一种可见光诱导的共轭磺酰胺串联脱砜/环化,合成全氟烷基化吲哚酮或α-芳基酰胺的方法。此反应以多氟烷基碘或溴为氟源,在发光二极管蓝光灯照射下,利用面式-三(2-苯基吡啶)合铱催化N-烷基-N-甲基丙烯酰基苯磺酰胺经过串联自由基加成/β-芳基迁移/脱砜环化过程,一步构筑两重碳-碳键,以41%~78%的产率合成了一系列含氟吲哚酮或α-芳基酰胺。此方法底物适用范围广,反应条件温和(室温),催化体系绿色,为具有潜在生理活性的含氟吲哚酮及α-芳基酰胺的合成提供了一条高效、快捷的新途径。

关键词: 共轭苯磺酰胺, 全氟烷基化, 串联环化, 光催化, 吲哚酮

Abstract:

A visible light induced desulfonylative cyclization cascade of N-sulfonylmethacrylamides toward perfluoroalkylated oxindoles and α-arylamides was developed. Under light-emitting diode(LED) irradiation, in the presence of fac-tris-2-phenylpyridine iridium(Ⅲ)(fac-Ir(ppy)₃) and perfluoroalkyl iodides or bromides, N-butyl-N-(tolylsulfonyl)methacrylamides underwent tandem radical addition/β-arylmigration/desulfonylation to construct two-fold of C—C bonds in single step, leading to a series of perfluoroalkylated oxindoles and α-aryl-β-perfluoroalkyl amide in 41%~78% yield. This mild catalytic protocol exhibits a broad substrate scope and therefore, provides a green and efficient approach to fluorinated oxindoles with potential biological activities.

Key words: N-sulfonylmethacrylamides, perfluoroalkylation, cascade cyclization, photoredox catalysis, oxindoles

李增增,袁莉,王良能,王硕文,余健,夏绿露,邓佑林,唐石. 可见光诱导的共轭磺酰胺串联脱砜/环化反应[J]. 应用化学, 2017, 34(11): 1287-1294.

LI Zengzeng,YUAN Li,WANG Liangneng,WANG Shuowen,YU Jian,XIA Lyulu,DENG Youlin,TANG Shi. Visible Light Induced Desulfonylative Annulation Cascade of N-Sulfonylmethacrylamides[J]. Chinese Journal of Applied Chemistry, 2017, 34(11): 1287-1294.

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